{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,7,30]],"date-time":"2025-07-30T15:48:45Z","timestamp":1753890525078,"version":"3.41.2"},"reference-count":66,"publisher":"Frontiers Media SA","license":[{"start":{"date-parts":[[2022,4,21]],"date-time":"2022-04-21T00:00:00Z","timestamp":1650499200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001807","name":"Funda\u00e7\u00e3o de Amparo \u00e0 Pesquisa do Estado de S\u00e3o Paulo","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100001807","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["frontiersin.org"],"crossmark-restriction":true},"short-container-title":["Front. Cell. Infect. Microbiol."],"abstract":"<jats:p>Malaria is one of the most widespread parasitic diseases, especially in Africa, Southeast Asia and South America. One of the greatest problems for control of the disease is the emergence of drug resistance, which leads to a need for the development of new antimalarial compounds. The biosynthesis of isoprenoids has been investigated as part of a strategy to identify new targets to obtain new antimalarial drugs. Several isoprenoid quinones, including menaquinone-4 (MK-4\/vitamin K2), \u03b1- and \u03b3-tocopherol and ubiquinone (UQ) homologs UQ-8 and UQ-9, were previously detected in <jats:italic>in vitro<\/jats:italic> cultures of <jats:italic>Plasmodium falciparum<\/jats:italic> in asexual stages. Herein, we described for the first time the presence of phylloquinone (PK\/vitamin K1) in <jats:italic>P. falciparum<\/jats:italic> and discuss the possible origins of this prenylquinone. While our results in metabolic labeling experiments suggest a biosynthesis of PK prenylation <jats:italic>via<\/jats:italic> phytyl pyrophosphate (phytyl-PP) with phytol being phosphorylated, on the other hand, exogenous PK attenuated atovaquone effects on parasitic growth and respiration, showing that this metabolite can be transported from extracellular environment and that the mitochondrial electron transport system (ETS) of <jats:italic>P. falciparum<\/jats:italic> is capable to interact with PK. Although the natural role and origin of PK remains elusive, this work highlights the PK importance in plasmodial metabolism and future studies will be important to elucidate in seeking new targets for antimalarial drugs.<\/jats:p>","DOI":"10.3389\/fcimb.2022.869085","type":"journal-article","created":{"date-parts":[[2022,4,21]],"date-time":"2022-04-21T11:07:51Z","timestamp":1650539271000},"update-policy":"https:\/\/doi.org\/10.3389\/crossmark-policy","source":"Crossref","is-referenced-by-count":2,"title":["Presence of Phylloquinone in the Intraerythrocytic Stages of Plasmodium falciparum"],"prefix":"10.3389","volume":"12","author":[{"given":"Rodrigo A. C.","family":"Sussmann","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Heloisa B.","family":"Gabriel","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Alejandro Garc\u00eda","family":"R\u00edos","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Danielle S.","family":"Menchaca Vega","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Lydia F.","family":"Yamaguchi","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Antonio","family":"Dom\u00e9nech-Carb\u00f3","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Gerardo","family":"Cebri\u00e1n-Torrej\u00f3n","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Emilia A.","family":"Kimura","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Massuo J.","family":"Kato","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ignasi","family":"Bofill Verdaguer","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Marcell","family":"Crispim","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Alejandro M.","family":"Katzin","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1965","published-online":{"date-parts":[[2022,4,21]]},"reference":[{"key":"B1","doi-asserted-by":"publisher","DOI":"10.2174\/1389557516666160623082714","article-title":"Phylloquinone (Vitamin K1): Occurrence, Biosynthesis and Functions","volume":"17","author":"Basset","year":"2017","journal-title":"Mini-Rev. Med. Chem."},{"key":"B2","doi-asserted-by":"publisher","first-page":"S41","DOI":"10.1016\/j.mito.2007.02.006","article-title":"The Antioxidant Role of Coenzyme Q","volume":"7","author":"Bentinger","year":"2007","journal-title":"Mitochondrion"},{"key":"B3","doi-asserted-by":"publisher","first-page":"116","DOI":"10.1016\/j.bbagen.2007.09.006","article-title":"Participation of Chlorobiumquinone in the Transplasma Membrane Electron Transport System of Leishmania Donovani Promastigote: Effect of Near-Ultraviolet Light on the Redox Reaction of Plasma Membrane","volume":"1780","author":"Biswas","year":"2008","journal-title":"Biochim. Biophys. Acta - Gen. Subj."},{"key":"B4","doi-asserted-by":"publisher","first-page":"33","DOI":"10.1016\/0166-6851(86)90140-4","article-title":"In Vivo Time Course of Synthesis and Processing of Major Schizont Membrane Polypeptides in Plasmodium Falciparum","volume":"20","author":"Braun-Breton","year":"1986","journal-title":"Mol. Biochem. Parasitol"},{"key":"B5","doi-asserted-by":"publisher","first-page":"373","DOI":"10.1006\/expr.1995.1049","article-title":"Interactions of Atovaquone With Other Antimalarial Drugs Against Plasmodium Falciparum In Vitro","volume":"80","author":"Canfield","year":"1995","journal-title":"Exp. Parasitol."},{"key":"B6","doi-asserted-by":"publisher","first-page":"51749","DOI":"10.1074\/jbc.M408360200","article-title":"The Methylerythritol Phosphate Pathway is Functionally Active in All Intraerythrocytic Stages of Plasmodium Falciparum","volume":"279","author":"Cassera","year":"2004","journal-title":"J. Biol. Chem."},{"key":"B7","doi-asserted-by":"publisher","first-page":"151","DOI":"10.1016\/0022-0728(90)87142-7","article-title":"Characterization of Iron Tetrakis(N-Methyl-2-Pyridyl)Porphine in Aqueous Media: Electrochemical Generation of Stable Iron(I), Iron(II), Iron(III) and Iron(IV) Porphyrins at Room Temperature","volume":"294","author":"Chen","year":"1990","journal-title":"J. Electroanal. Chem. Interfacial Electrochem."},{"key":"B8","doi-asserted-by":"publisher","first-page":"161","DOI":"10.1080\/00034983.1939.11685064","article-title":"Experiments With Isolated Malaria Parasites (Plasmodium Knowlesi) Free From Red Cells","volume":"33","author":"Christophers","year":"1939","journal-title":"Ann. Trop. Med. Parasitol."},{"key":"B9","doi-asserted-by":"publisher","first-page":"221","DOI":"10.1099\/00221287-100-2-221","article-title":"Distribution of Menaquinones in Actinomycetes and Corynebacteria","volume":"100","author":"Collins","year":"1977","journal-title":"J. Gen. Microbiol."},{"key":"B10","doi-asserted-by":"publisher","first-page":"7579","DOI":"10.1021\/ja051151a","article-title":"Electrochemical Reduction of NO by Hemin Adsorbed at Pyrolitic Graphite","volume":"127","author":"de Groot","year":"2005","journal-title":"J.\u00a0Am. Chem. Soc"},{"key":"B11","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.16.6.710","article-title":"Quantitative Assessment of Antimalarial Activity In Vitro by a Semiautomated Microdilution Technique","volume":"16","author":"Desjardins","year":"1979","journal-title":"Antimicrob. Agents Chemother"},{"key":"B12","doi-asserted-by":"publisher","first-page":"609","DOI":"10.1351\/PAC-REP-11-11-13","article-title":"Electroanalytical Chemistry for the Analysis of Solids: Characterization and Classification (IUPAC Technical Report)","volume":"85","author":"Dom\u00e9nech-Carb\u00f3","year":"2013","journal-title":"Pure Appl. Chem."},{"key":"B13","doi-asserted-by":"publisher","first-page":"4014","DOI":"10.1021\/ac303746k","article-title":"Solid-State Electrochemical Assay of Heme-Binding Molecules for Screening of Drugs With Antimalarial Potential","volume":"85","author":"Dom\u00e9nech-Carb\u00f3","year":"2013","journal-title":"Anal. Chem."},{"key":"B14","doi-asserted-by":"publisher","first-page":"972","DOI":"10.1016\/j.bmcl.2008.11.071","article-title":"Type II NADH Dehydrogenase of the Respiratory Chain of Plasmodium Falciparum and its Inhibitors","volume":"19","author":"Dong","year":"2009","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"B15","doi-asserted-by":"publisher","first-page":"296","DOI":"10.1016\/0169-4758(94)90079-5","article-title":"Coenzyme Q Homologs in Parasitic Protozoa as Targets for Chemotherapeutic Attack","volume":"10","author":"Ellis","year":"1994","journal-title":"Parasitol. Today"},{"key":"B16","doi-asserted-by":"publisher","DOI":"10.3109\/10715769709084478","article-title":"Antioxidant Activity of Reduced Menadione in Solvent Solution and in Model Membranes","volume":"26","author":"Fiorentini","year":"1997","journal-title":"Free Radic. Res"},{"key":"B17","doi-asserted-by":"publisher","DOI":"10.1007\/BF00269302","article-title":"Prenylation and Methylation Reactions in Phylloquinone (Vitamin K1) Synthesis in Capsicum Annuum Plastids","volume":"6","author":"Gaudilli\u00e8re","year":"1984","journal-title":"Plant Cell Rep"},{"key":"B18","unstructured":"Saccharomyces Cerevisiae Sec59 Cells are Deficient in Dolichol Kinase Activity\n            HellerL.\n            OrleanP.\n            AdairW. L.\n          1992"},{"key":"B19","doi-asserted-by":"publisher","DOI":"10.1128\/JB.187.6.1937-1944.2005","article-title":"Menaquinone-Specific Prenyl Reductase From the Hyperthermophilic Archaeon Archaeoglobus Fulgidus","volume":"187","author":"Hemmi","year":"2005","journal-title":"J. Bacteriol."},{"key":"B20","doi-asserted-by":"publisher","first-page":"66","DOI":"10.1016\/0169-4758(93)90040-M","article-title":"Atovaquone - a Novel Broad-Spectrum Anti-Infective Drug","volume":"9","author":"Hudson","year":"1993","journal-title":"Parasitol. Today"},{"key":"B21","doi-asserted-by":"publisher","first-page":"1036","DOI":"10.1006\/bbrc.1994.1554","article-title":"Phosphorylation of Farnesol by a Cell-Free System From Botryococcus Braunii","volume":"200","author":"Inoue","year":"1994","journal-title":"Biochem. Biophys. Res. Commun."},{"key":"B22","doi-asserted-by":"publisher","first-page":"2470","DOI":"10.1074\/jbc.M509222200","article-title":"A Salvage Pathway for Phytol Metabolism in Arabidopsis","volume":"281","author":"Ischebeck","year":"2006","journal-title":"J. Biol. Chem."},{"key":"B23","doi-asserted-by":"publisher","first-page":"10949","DOI":"10.1073\/pnas.1003335107","article-title":"A Common Red Algal Origin of the Apicomplexan, Dinoflagellate, and Heterokont Plastids","volume":"107","author":"Janouskovec","year":"2010","journal-title":"Proc. Natl. Acad. Sci."},{"key":"B24","doi-asserted-by":"publisher","first-page":"4843","DOI":"10.1021\/ic00049a023","article-title":"Redox Chemistry of Water-Soluble Iron, Manganese, and Chromium Metalloporphyrins and Acid-Base Behavior of Their Lyate Axial Ligands in Aqueous Solution: Influence of Electronic Effects","volume":"31","author":"Jeon","year":"1992","journal-title":"Inorg. Chem."},{"key":"B25","doi-asserted-by":"publisher","first-page":"219","DOI":"10.1038\/16618","article-title":"Shikimate Pathway in Apicomplexan Parasites","volume":"397","author":"Keeling","year":"1999","journal-title":"Nature"},{"key":"B26","doi-asserted-by":"publisher","DOI":"10.2307\/3280287","article-title":"Synchronization of Plasmodium Falciparum Erythrocytic Stages in Culture","volume":"65","author":"Lambros","year":"1979","journal-title":"J. Parasitol"},{"key":"B27","doi-asserted-by":"publisher","first-page":"13172","DOI":"10.1073\/pnas.240454797","article-title":"Isoprenoid Biosynthesis: The Evolution of Two Ancient and Distinct Pathways Across Genomes","volume":"97","author":"Lange","year":"2000","journal-title":"Proc. Natl. Acad. Sci. U. S. A."},{"key":"B28","doi-asserted-by":"publisher","first-page":"7617","DOI":"10.1021\/ja00231a006","article-title":"Single Electron Transfer and Nucleophilic Substitution. Reaction of Alkyl Bromides With Aromatic Anion Radicals and Low Oxidation State Iron Porphyrins","volume":"110","author":"Lexa","year":"1988","journal-title":"J. Am. Chem. Soc"},{"key":"B29","doi-asserted-by":"publisher","first-page":"73","DOI":"10.1002\/biof.5520180209","article-title":"Phylloquinone, What can We Learn From Plants","volume":"18","author":"Lochner","year":"2003","journal-title":"BioFactors"},{"key":"B30","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1186\/s13068-018-1342-2","article-title":"Discovery of Novel Geranylgeranyl Reductases and Characterization of Their Substrate Promiscuity","volume":"11","author":"Meadows","year":"2018","journal-title":"Biotechnol. Biofuels."},{"key":"B31","doi-asserted-by":"publisher","first-page":"G112","DOI":"10.1149\/2.032210jes","article-title":"Redox Behavior of a Derivative of Vitamin K at a Glassy Carbon Electrode","volume":"159","author":"Munir","year":"2012","journal-title":"J.\u00a0Electrochem. Soc."},{"key":"B32","doi-asserted-by":"publisher","first-page":"112","DOI":"10.1006\/expr.1997.4194","article-title":"Plasmodium Falciparum: Cyanide-Resistant Oxygen Consumption","volume":"87","author":"Murphy","year":"1997","journal-title":"Exp. Parasitol"},{"key":"B33","doi-asserted-by":"publisher","first-page":"203","DOI":"10.1007\/s10863-011-9347-6","article-title":"Involvement of Thermoplasmaquinone-7 in Transplasma Membrane Electron Transport of Entamoeba Histolytica Trophozoites: A Key Molecule for Future Rational Chemotherapeutic Drug Designing","volume":"43","author":"Nandi","year":"2011","journal-title":"J. Bioenerg. Biomembr."},{"key":"B34","doi-asserted-by":"publisher","first-page":"1587","DOI":"10.1016\/j.bbabio.2010.06.007","article-title":"Occurrence, Biosynthesis and Function of Isoprenoid Quinones","volume":"1797","author":"Nowicka","year":"2010","journal-title":"Biochim. Biophys. Acta - Bioenerg."},{"key":"B35","doi-asserted-by":"publisher","first-page":"57","DOI":"10.1007\/978-1-4615-5901-6_3","article-title":"Polyprenyl Diphosphate Synthases","volume":"28","author":"Ogura","year":"1997","journal-title":"Subcell. Biochem."},{"key":"B36","doi-asserted-by":"publisher","first-page":"88","DOI":"10.1038\/nature05572","article-title":"Specific Role of Mitochondrial Electron Transport in Blood-Stage Plasmodium Falciparum","volume":"446","author":"Painter","year":"2007","journal-title":"Nature"},{"key":"B37","doi-asserted-by":"publisher","DOI":"10.1038\/nprot.2009.198","article-title":"Synchronous Culture of Plasmodium Falciparum at High Parasitemia Levels","volume":"4","author":"Radfar","year":"2009","journal-title":"Nat. Protoc"},{"key":"B38","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1186\/1475-2875-7-45","article-title":"Concentration and Purification by Magnetic Separation of the Erythrocytic Stages of All Human Plasmodium Species","volume":"7","author":"Ribaut","year":"2008","journal-title":"Malar. J"},{"key":"B39","doi-asserted-by":"publisher","DOI":"10.1016\/S0166-6851(97)00237-5","article-title":"Implications of Mycoplasma Contamination in Plasmodium Falciparum Cultures and Methods for its Detection and Eradication","volume":"92","author":"Rowe","year":"1998","journal-title":"Mol. Biochem. Parasitol"},{"key":"B40","doi-asserted-by":"publisher","first-page":"2835","DOI":"10.1021\/jp981160o","article-title":"Electroreflectance Study of Hemin Adsorbed on a HOPG Electrode: Estimation of Molecular Orientation and Analysis of Nonfaradaic Electroreflectance Signal Due to the Stark Effect","volume":"102","author":"Sagara","year":"1998","journal-title":"J. Phys. Chem. B"},{"key":"B41","doi-asserted-by":"publisher","DOI":"10.1016\/j.jmb.2011.04.002","article-title":"Structure and Mutation Analysis of Archaeal Geranylgeranyl Reductase","volume":"409","author":"Sasaki","year":"2011","journal-title":"J. Mol. Biol"},{"key":"B42","doi-asserted-by":"publisher","DOI":"10.1042\/bj0970766","article-title":"Isolation of a Naphthaquinone With Partly Hydrogenated Side Chain From Corynebacterium Diphtheriae","volume":"97","author":"Scholes","year":"1965","journal-title":"Biochem. J"},{"key":"B43","doi-asserted-by":"publisher","first-page":"161","DOI":"10.1016\/S1937-6448(10)81005-6","article-title":"Metabolic Pathways in the Apicoplast of Apicomplexa","volume":"281","author":"Seeber","year":"2010","journal-title":"Int. Rev. Cell Mol. Biol"},{"key":"B44","doi-asserted-by":"publisher","first-page":"92","DOI":"10.1016\/0268-960X(92)90011-E","article-title":"Vitamin K Metabolism and Nutriture","volume":"6","author":"Shearer","year":"1992","journal-title":"Blood Rev."},{"key":"B45","doi-asserted-by":"publisher","first-page":"182","DOI":"10.3945\/an.111.001800","article-title":"Vitamin K Nutrition, Metabolism, and Requirements: Current Concepts and Future Research","volume":"3","author":"Shearer","year":"2012","journal-title":"Adv. Nutr."},{"key":"B46","doi-asserted-by":"publisher","first-page":"602","DOI":"10.1021\/jm00298a004","article-title":"Coenzyme Q. CXXII. Identification of Ubiquinone-8 Biosynthesized by Plasmodium Knowlesi, P. Cynomolgi, and P. Berghei","volume":"13","author":"Skelton","year":"1970","journal-title":"J. Med. Chem."},{"key":"B47","doi-asserted-by":"publisher","first-page":"1803","DOI":"10.1128\/AAC.48.5.1803-1806.2004","article-title":"Simple and Inexpensive Fluorescence-Based Technique for High-Throughput Antimalarial Drug Screening","volume":"48","author":"Smilkstein","year":"2004","journal-title":"Antimicrob. Agents Chemother."},{"key":"B48","doi-asserted-by":"publisher","first-page":"1817","DOI":"10.1099\/13500872-145-8-1817","article-title":"Microbial Ubiquinones: Multiple Roles in Respiration, Gene Regulation and Oxidative Stress Management","volume":"145","author":"Soballe","year":"1999","journal-title":"Microbiology"},{"key":"B49","doi-asserted-by":"publisher","first-page":"800","DOI":"10.1021\/acsinfecdis.6b00106","article-title":"Biosynthesis and Regulation of Sulfomenaquinone, a Metabolite Associated With Virulence in Mycobacterium Tuberculosis","volume":"2","author":"Sogi","year":"2016","journal-title":"ACS Infect. Dis."},{"key":"B50","doi-asserted-by":"publisher","first-page":"3985","DOI":"10.1016\/j.febslet.2011.11.005","article-title":"Intraerythrocytic Stages of Plasmodium Falciparum Biosynthesize Vitamin E","volume":"585","author":"Sussmann","year":"2011","journal-title":"FEBS Lett."},{"key":"B51","doi-asserted-by":"publisher","first-page":"368","DOI":"10.1016\/j.jchromb.2016.09.011","article-title":"Stabilization and Detection of Hydrophylloquinone as Di- O -Methyl Derivative","author":"Sussmann","year":"2016","journal-title":"J.\u00a0Chromatogr. B"},{"key":"B52","doi-asserted-by":"publisher","first-page":"461","DOI":"10.1186\/s13071-017-2402-3","article-title":"Plasmodium Falciparum Uses Vitamin E to Avoid Oxidative Stress","volume":"10","author":"Sussmann","year":"2017","journal-title":"Parasites Vectors"},{"key":"B53","doi-asserted-by":"publisher","first-page":"107","DOI":"10.1042\/bj1060107","article-title":"Biosynthesis of Phytoquinones. Incorporation of L-[Me-14c,3h]Methionine Into Terpenoid Quinones and Chromanols in Maize Shoots","volume":"106","author":"Threlfall","year":"1968","journal-title":"Biochem. J."},{"key":"B54","doi-asserted-by":"publisher","first-page":"133","DOI":"10.1016\/0022-0728(90)87035-I","article-title":"The Electrochemistry of Hemin in Dimethylsulfoxide","volume":"281","author":"Tieman","year":"1990","journal-title":"J. Electroanal. Chem."},{"key":"B55","doi-asserted-by":"publisher","first-page":"251","DOI":"10.1016\/0378-1097(89)90405-9","article-title":"Fully Saturated Menaqionones in the Archaebacterium Pyrobaculum Islandicum","volume":"60","author":"Tindall","year":"1989","journal-title":"FEMS Microbiol. Lett"},{"key":"B56","doi-asserted-by":"publisher","first-page":"4761","DOI":"10.1016\/j.febslet.2010.10.055","article-title":"Intraerythrocytic Stages of Plasmodium Falciparum Biosynthesize Menaquinone","volume":"584","author":"Tonhosolo","year":"2010","journal-title":"FEBS Lett."},{"key":"B57","doi-asserted-by":"publisher","first-page":"673","DOI":"10.1126\/science.781840","article-title":"Human Malaria Parasites in Continuous Culture","volume":"193","author":"Trager","year":"1976","journal-title":"Science"},{"key":"B58","doi-asserted-by":"publisher","first-page":"292","DOI":"10.1021\/acscentsci.5b00212","article-title":"Partial Saturation of Menaquinone in Mycobacterium Tuberculosis: Function and Essentiality of a Novel Reductase, Menj","volume":"1","author":"Upadhyay","year":"2015","journal-title":"ACS Cent. Sci"},{"key":"B59","doi-asserted-by":"publisher","first-page":"212","DOI":"10.1105\/tpc.105.037077","article-title":"The Arabidopsis Vitamin E Pathway Gene5-1 Mutant Reveals a Critical Role for Phytol Kinase in Seed Tocopherol Biosynthesis","volume":"18","author":"Valentin","year":"2006","journal-title":"Plant Cell Online"},{"key":"B60","doi-asserted-by":"publisher","first-page":"405","DOI":"10.1111\/j.1365-2958.2005.04699.x","article-title":"Development of the Endoplasmic Reticulum, Mitochondrion and Apicoplast During the Asexual Life Cycle of Plasmodium Falciparum","volume":"57","author":"van Dooren","year":"2005","journal-title":"Mol. Microbiol."},{"key":"B61","doi-asserted-by":"publisher","first-page":"3721","DOI":"10.3390\/molecules24203721","article-title":"Prenylquinones in Human Parasitic Protozoa: Biosynthesis, Physiological Functions, and Potential as Chemotherapeutic Targets","volume":"24","author":"Verdaguer","year":"2019","journal-title":"Molecules"},{"key":"B62","doi-asserted-by":"publisher","DOI":"10.1016\/S0006-2952(97)00254-2","article-title":"The Potent Antioxidant Activity of the Vitamin K Cycle in Microsomal Lipid Peroxidation","volume":"54","author":"Vervoort","year":"1997","journal-title":"Biochem. Pharmacol"},{"key":"B63","doi-asserted-by":"publisher","first-page":"188","DOI":"10.1002\/tcr.201100005","article-title":"Voltammetry of the Liposoluble Vitamins (a, D, E and K) in Organic Solvents","volume":"12","author":"Webster","year":"2012","journal-title":"Chem. Rec."},{"volume-title":"WHO | the World Malaria Report 2021","year":"2021","key":"B64"},{"key":"B65","doi-asserted-by":"publisher","first-page":"1443","DOI":"10.1093\/plphys\/kiab031","article-title":"Plasma Membrane Phylloquinone Biosynthesis in Nonphotosynthetic Parasitic Plants","volume":"185","author":"Xi","year":"2021","journal-title":"Plant Physiol."},{"key":"B66","doi-asserted-by":"publisher","first-page":"1145","DOI":"10.1002\/(sici)1521-4109(199911)11:15<1145:aid-elan1145>3.3.co;2-#","article-title":"Electrochemical Studies of Vitamin K3 Interacting With Hemoglobin and Determination of Hemoglobin","volume":"11","author":"Zhu","year":"1999","journal-title":"Electroanalysis"}],"container-title":["Frontiers in Cellular and Infection Microbiology"],"original-title":[],"link":[{"URL":"https:\/\/www.frontiersin.org\/articles\/10.3389\/fcimb.2022.869085\/full","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2022,4,21]],"date-time":"2022-04-21T11:07:56Z","timestamp":1650539276000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.frontiersin.org\/articles\/10.3389\/fcimb.2022.869085\/full"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,4,21]]},"references-count":66,"alternative-id":["10.3389\/fcimb.2022.869085"],"URL":"https:\/\/doi.org\/10.3389\/fcimb.2022.869085","relation":{},"ISSN":["2235-2988"],"issn-type":[{"type":"electronic","value":"2235-2988"}],"subject":[],"published":{"date-parts":[[2022,4,21]]},"article-number":"869085"}}